1-Butyne → 1-But-1-ynyl-4-fluoro-2-methoxymethoxy-benzene

HRID 423179

반응식

HRID 423179 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH2:10][O:11][CH3:12].[CH:13]#[C:14][CH2:15][CH3:16]>C(NCC)C.CCOCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:13]([C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[O:9][CH2:10][O:11][CH3:12])#[C:14][CH2:15][CH3:16]

참가 물질

7

반응물 2

HCID 78461-ButyneHCID 108236251-Bromo-4-fluoro-2-(methoxymethoxy)benzene

생성물 1

HCID 595651761-But-1-ynyl-4-fluoro-2-methoxymethoxy-benzene수율 91%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 3283Diethyl Ether용매HCID 8021Diethylamine용매

반응 조건

온도
70 °C

실험 절차

1-Bromo-4-fluoro-2-methoxymethoxy-benzene (7.6 g, 32 mmol) is placed in a pressure flask, dissolved in diethylamine (65 mL) and degassed with nitrogen for 15 min. An excess of butyne is bubbled through the solution, CuI (1.9 g, 10 mmol) and PdCl2(PPh3)2 (2.3 g, 3.3 mmol) are added, and the flask is heated to 70° C. for 44 h. The mixture is diluted with ether, then washed with saturated aqueous NH4Cl and brine. The organic portion is dried over MgSO4, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (Biotage® Si65M, 3% THF/hexane) to provide 6.12 g (91%) of the title compound as an orange solid. GCMS m/e 208 [M]+.

후처리

  1. customdegassed with nitrogen for 15 min
  2. additionare added
  3. washwashed with saturated aqueous NH4Cl and brine
  4. dry with materialThe organic portion is dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by flash chromatography (Biotage® Si65M, 3% THF/hexane)

출처 및 근거

ORD 기록
ord-bc3a652c23944c49801cf9ef32298cc6
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101761B2

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